Generation and rearrangement of C2-symmetric chiral allyl anions derived from dibenzo- and 1,1'-dinaphtho-2,2'-dithiopropenes

The allyl anions generated from 4H-dinaphtho[2,1-f:1?,2?-h][1,5]dithionin (6) and 2-ethenyl-dinaphtho[2,1-d:1?,2?-f][1, (8) rearranged both to the thiolate 10 which further reacted with water or methyl iodide to afford 9 or 12 respectively. A similar behavior was exhibited by the anion of 4H-dibenzo[f,h][1,5]dithionin (15). © 1991.